Sidi Gor Tex Adventure boots, all day comfort and great protection followed closely by the leather man multi tool, has helped me constantly both supplied by my completely supportive wife (think she just likes me out of the house )

Luggage: Aerostich Courier's bag. Two weeks into my first college quarter, I'd nearly torn out the straps of a then-new Jansport backpack. So I bought a Courier's Bag from 'stich. A year of college couldn't kill it despite loading the damn thing to ~40 lbs at times. My books and laptop came through with minimal wear, too. I'm headed back here in a few weeks to start my second year, and the bag is going with me. It still looks new on the inside, and it's still waterproof. The only peeve: it can't carry everything. I'd like to get a Happy Trails 47L top box to remedy this, but as long as college makes my wallet scream in terror, it will have to wait. For everything else, this bag does any job I've demanded of it. Got mine in Hi-Viz.

Misc: Sea Foam. Stabilizes the gas better than Sta-Bil, and it degunks the carbs. The pilot jets on my V-Star 650 will start to plug up if it sits for a week or two. Every time I fill the tank, I put a good splash of Sea Foam in too. At $7-8 a can, it's cheap insurance that the bike will always go. Especially since there are times when I don't know how long the bike will sit.

Safety: EXO-700 helmet in Chernobyl Green. Seeing cagers blink stupidly as I ride around town wearing this bucket - on a cruiser - is simply priceless! It works as well as the SMIDSY weave in getting people to see me. Decent vents and a nice fit, too. Damn shame Scorpion dropped the color, though.

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Christopher Robin was sitting outside his door, putting on his Big Boots.
As soon as he saw the Big Boots, Pooh knew that an Adventure was going to happen

Smart wool/Merino wool underwear. I got a single pair about 7 months ago and they've been my favorite meaning they get worn about 1/2 the time. (I know... too much info!)

I don't have experience with them in the cold (live in Malaysia where it's hot and humid) but they seem great in hot, humid weather. My favorite before was ex-officio's synthetic boxers. I wear them for riding, hiking, anything... often my jungle rides include miles of hot, sweaty work on foot, hiking hills building bamboo bridges.

They stay wet longer than ex-officio synthetics BUT they are more comfortable to wear wet. (Of course I'd rather have any dry pair than a wet pair but they are the most comfortable wet and any dry pair quickly become wet in the jungle!)
They dry faster than cotton but not as fast as the synthetic ex oficios.
You'll get chaffing anytime you run/hike miles in a wet underwear BUT these are the best in that situation in my experience.
They feel the coolest in hot weather between synthetic, cotton and wool.
They do wear out faster and are expensive.